Sulfuryl chloride

Short description: Chemical compound

Sulfuryl chloride

Names
IUPAC name

Sulfuryl chloride

Other names

Sulfonyl chloride
Sulfuric chloride
Sulfur dichloride dioxide

Identifiers

CAS Number

* 7791-25-5 Y

3D model (JSmol)

* Interactive image

ChEBI |

* CHEBI:29291 Y

ChEMBL |

* ChEMBL3186735

ChemSpider |

* 23050 Y

EC Number |

* 232-245-6

Gmelin Reference

| 2256

PubChem CID

* 24648

RTECS number |

* WT4870000

UNII |

* JD26K0R3J1 Y

UN number | 1834

InChI

* InChI=1S/Cl2O2S/c1-5(2,3)4 Y

Key: YBBRCQOCSYXUOC-UHFFFAOYSA-N Y

* InChI=1/Cl2O2S/c1-5(2,3)4

Key: YBBRCQOCSYXUOC-UHFFFAOYAD

SMILES

* ClS(Cl)(=O)=O

Properties

Chemical formula

| SO2Cl2
Molar mass | 134.9698 g mol−1
Appearance  | Colorless liquid with a pungent odor. Yellows upon standing.
Density | 1.67 g cm−3 (20 °C)
Melting point |  −54.1 °C (−65.4 °F; 219.1 K)
Boiling point |  69.4 °C (156.9 °F; 342.5 K)

Solubility in water

| hydrolyzes
Solubility | miscible with benzene, toluene, chloroform, CCl4, glacial acetic acid

Refractive index (nD)

| 1.4437 (20 °C)[1]
Hazards
GHS pictograms |
GHS Signal word | Danger

GHS hazard statements

| H314, H335

GHS precautionary statements

| P260, P261, P264, P271, P280, P301+330+331, P303+361+353, P304+340, P305+351+338, P310, P312, P321, P363, P403+233, P405, P501
NFPA 704 (fire diamond)  |

~~W~~

Flash point | Not flammable
Related compounds

Related sulfuryl halides

| Sulfuryl fluoride

Related compounds

| Thionyl chloride
Chlorosulfonic acid
Sulfuric acid
Chromyl chloride

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Y verify (what is YN ?)
Infobox references

Tracking categories (test):

* SizeSet

Sulfuryl chloride is an inorganic compound with the formula SO2Cl2. At room temperature, it is a colorless liquid with a pungent odor. Sulfuryl chloride is not found in nature.

Sulfuryl chloride is commonly confused with thionyl chloride, SOCl2. The properties of these two sulfur oxychlorides are quite different: sulfuryl chloride is a source of chlorine whereas thionyl chloride is a source of chloride ions. An alternative IUPAC name is sulfuryl dichloride.

Sulfur is tetrahedral in SO2Cl2 and the oxidation state of the sulfur atom is +6, as in sulfuric acid.

## Contents

* 1 Synthesis
* 1.1 Legacy routes
* 2 Reactions
* 3 Uses
* 4 Precautions
* 5 See also
* 6 References
* 7 Further reading

## Synthesis

SO2Cl2 is prepared by the reaction of sulfur dioxide and chlorine in the presence of a catalyst, such as activated carbon.[2]

SO2 \+ Cl2 → SO2Cl2

The product can be purified by fractional distillation.

### Legacy routes

Sulfuryl chloride was first prepared in 1838 by the French chemist Henri Victor Regnault.[3]

Older routes include oxidation of thionyl chloride:

5 SOCl2 \+ HgO → ClSSCl + HgCl2 \+ 3 SO2Cl2
2 SOCl2 \+ MnO2 → SO2 \+ MnCl2 \+ SO2Cl2

## Reactions

Sulfuryl chloride reacts with water, releasing hydrogen chloride gas and sulfuric acid:

2 H2O + SO2Cl2 → 2 HCl + H2SO4

For sulfuryl chloride, this happens at room temperature, but the related sulfuryl fluoride does not hydrolyse at temperatures up to 150 °C.

SO2Cl2 will also decompose when heated to or above 100 °C, about 30 °C above its boiling point.

Upon standing, SO2Cl2 decomposes to sulfur dioxide and chlorine, which gives the older samples a slightly yellowish color.[2]

SO2Cl2 can be used as a source of chlorine in alkane radical chlorination, initiated chemically (usually by peroxide) or by light:[4]

CH4 \+ SO2Cl2 → CH3Cl + SO2 \+ HCl

## Uses

Sulfuryl chloride is used as a source of Cl2. Because it is a pourable liquid, it is considered more convenient than Cl2 to dispense.

Sulfuryl chloride is used in the conversion of C−H to C−Cl adjacent to activating substituents such as carbonyls and sulfoxides:[5][6]

RC(O)CH
2R' + SO
2Cl
2 → RC(O)CHClR' + HCl + SO

It also chlorinates alkanes, alkenes, alkynes, aromatics, ethers (such as tetrahydrofuran) and epoxides. Such reactions occur under free radical conditions using an initiator such as AIBN. It convert thiols or disulfides into the corresponding sulfenyl chlorides:[7]

RSH + SO
2Cl
2 → RSCl + HCl + SO

Occasionally, sulfinyl chlorides result from such reactions.[8] SO2Cl2 can also convert alcohols to alkyl chlorides. In industry, sulfuryl chloride is most used in producing pesticides. Phosphorus pentachloride is prepared by the reaction of white phosphorus with sulfuryl chloride.

Sulfuryl chloride can also be used to treat wool to prevent shrinking.

## Precautions

Sulfuryl chloride is toxic, corrosive, and acts as a lachrymator. It releases hydrogen chloride upon contact with water, as well as donor solvents such as dimethyl sulfoxide and dimethylformamide.

## See also

* Disulfuryl chloride
* Trisulfuryl chloride

## References

1. ↑ Patnaik, P. (2002). Handbook of Inorganic Chemicals. McGraw-Hill. ISBN 978-0-07-049439-8.
2. ↑ 2.0 2.1 F. Fehér (1963). "Sulfuryl Chloride". in G. Brauer. Handbook of Preparative Inorganic Chemistry, 2nd Ed.. 1. NY, NY: Academic Press. pp. 382–384.
3. ↑ Regnault, Victor (1838). "Sur l'acide chlorosulfurique et la sulfamide" (in fr). Annales de Chimie et de Physique. Série 2 69: 170–184. https://books.google.com/books?id=oSdCAAAAcAAJ&pg=PA170.
* Reprinted as: Regnault, Victor (1839). "Ueber die Chlorschwefelsäure und das Sulfamid" (in de). Journal für Praktische Chemie 18: 93–104. doi:10.1002/prac.18390180104. https://books.google.com/books?id=MdEPAAAAQAAJ&pg=PA93.
4. ↑ Basic Principles of Organic Chemistry.
5. ↑ Mark Lautens, Giliane Bouchain (2002). "[4+3] Cycloaddition in Water. Synthesis of 2,4-endo,endo-Dimethyl-8-oxabicyclo[3.2.1]oct-6-en-3-one". Organic Syntheses 79: 251. doi:10.15227/orgsyn.079.0251.
6. ↑ Cragoe, Jr, Edward J.; Robb, Charles M. (1960). "3-Hydroxyquinoline". Organic Syntheses 40: 54. doi:10.15227/orgsyn.040.0054.
7. ↑ Barrett, Anthony G. M.; Dhanak, Dashyant; Graboski, Gregory G.; Taylor, Sven J. (1990). "(Phenylthio)Nitromethane". Organic Syntheses 68: 8. doi:10.15227/orgsyn.068.0008.
8. ↑ Page, P. C. B.; Wilkes, R. D.; Reynolds, D. (1995). "Alkyl Chalcogenides: Sulfur-based Functional Groups". in Ley, Steven V.. Synthesis: Carbon with One Heteroatom Attached by a Single Bond. Comprehensive Organic Functional Group Transformations. Elsevier. pp. 113–276. ISBN 9780080423234. https://books.google.com/books?id=BPcxrmIgLKMC&pg=PA173.

* "Sulfuryl chloride CAS No.: 7791-25-5". OECD SIDS. UNEP Publications. 2004. http://www.chem.unep.ch/irptc/sids/OECDSIDS/7791255.pdf.
* Maynard, G. D. (2001). Encyclopedia of Reagents for Organic Synthesis. John Wiley & Sons. doi:10.1002/047084289X.rs140. ISBN 978-0471936237. http://onlinelibrary.wiley.com/o/eros/articles/rs140/frame.html.

## Further reading

* Lautens, M.; Bouchain, G. (2002). "[4+3] Cycloaddition in Water. Synthesis of 2,4-endo,endo-Dimethyl-8-Oxabicyclo[3.2.1]oct-6-en-3-one". Organic Syntheses 79: 251. doi:10.15227/orgsyn.079.0251.
* McKee, R. H.; Salls, C. M. (1924). "Sulfuryl Chloride". Industrial and Engineering Chemistry 16 (4): 351–353. doi:10.1021/ie50172a008.
* Moussa, V. N. (2012). "Sulfuryl Chloride: A Versatile Alternative to Chlorine". Australian Journal of Chemistry 65 (1): 95–96. doi:10.1071/CH11367.
* North, H. B. (1910). "The Action of Thionyl and Sulphuryl Chlorides on Mercury and Mercury Oxide". Journal of the American Chemical Society 32 (2): 184–187. doi:10.1021/ja01920a004. https://zenodo.org/record/2166706.
* North, H. B.; Hageman, A. G. (1913). "Some New Reactions with Thionyl Chloride". Journal of the American Chemical Society 35 (5): 543–546. doi:10.1021/ja02194a004.

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*[CID]: Compound ID
*[H314]: Causes severe skin burns and eye damage
*[H335]: May cause respiratory irritation
*[P260]: Do not breathe dust/fume/gas/mist/vapours/spray
*[P261]: Avoid breathing dust/fume/gas/mist/vapours/spray
*[P264]: Wash … thoroughly after handling
*[P271]: Use only outdoors or in a well-ventilated area
*[P280]: Wear protective gloves/protective clothing/eye protection/face protection
*[P301+330+331]: IF SWALLOWED: Rinse mouth. Do NOT induce vomiting
*[P303+361+353]: IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower
*[P304+340]: IF INHALED: Remove victim to fresh air and keep at rest in a position comfortable for breathing
*[P305+351+338]: IF IN EYES: Rinse continuously with water for several minutes. Remove contact lenses if present and easy to do – continue rinsing
*[P310]: Immediately call a POISON CENTER or doctor/physician
*[P312]: Call a POISON CENTER or doctor/physician if you feel unwell
*[P321]: Specific treatment (see … on this label)
*[P363]: Wash contaminated clothing before reuse
*[P403+233]: Store in a well ventilated place. Keep container tightly closed
*[P405]: Store locked up
*[P501]: Dispose of contents/container to …